Weekend Watch List: 5 Must-Watch Movies for Entrepreneurs

Have you ever watched a film that left you a different person? Hollywood has a way of capturing reality and with it, our imagination. Here’s our pick of movies to watch -- wherever you are in your journey as an entrepreneur.

Wall Street [1987]

Rookie stockbroker Bud Fox meets his hero, Wall Street power player Gordon Gekko, by finagling his way into the latter’s office. Desperate to impress, Fox passes Gekko an insider tip he got from his father. He then gets taken under the older man’s wing, acting as his info lackey in a cat-and-mouse game of insider trading.

Directed by Oliver Stone, Wall Street is all about Gordon Gekko. Michael Douglas plays the cutthroat corporate raider who buys companies only to liquidate them for the big bucks. Gekko’s famous declaration that “greed is good” captures 1980s success in a nutshell.

Boiler Room [2000]

Seth Davis makes a tidy income running an unlicensed casino in his apartment until his father, a federal judge, finds out about it. So he gets a job at J.T. Marlin, selling dicey stocks by using high-pressure tactics over the phone. He turns out to be pretty good at it until he finally learns how the firm actually makes money.

Viewed as a homage to Wall Street but set to rap music, Boiler Room doesn’t feature a slick Gordon Gekko mentor. What it has instead is a pack of white young dudes who know how to work the phones, pumped by the promise of earning their first cool million. Here’s Ben Affleck’s memorable intro speech to the firm’s new trainees:

Wolf of Wall Street [2013]

A story about the rise and fall of a wayward stockbroker, Wolf of Wall Street is adapted from the memoir by Jordan Belfort. Belfort built a fortune in the 1980s and 90s by selling penny stocks, using the pump and dump method seen in the Boiler Room: hype up the value of worthless stocks, then sell it at a big profit, at which point the value drops and investors lose their money.

Directed by Martin Scorsese, the film runs at three hours and is one of Scorsese’s most entertaining depictions of excess and debauched lifestyle in a mad quest for more and more money. Leonardo DiCaprio plays the charismatic Belfort and nowhere does he nail the part as good as in the notorious sales pitch scene:

There Will Be Blood [2007]

Loosely based on Oil!, Upton Sinclair’s 1927 novel about a corrupt oil family, There Will Be Blood is dominated from beginning to end by the larger-than-life oil man Daniel Plainview. To become enormously wealthy is Plainview’s sole obsession in life. This practically renders the people around him as mere means to his ambition, including his adopted son.

Plainview’s epic greed overshadows everything in the stark landscape of the oil-rich California desert, including the compelling rhetoric of Eli Sunday, a preacher whom Plainview locked horns with early on. The film’s brutally violent scene between the two is one of the unforgettable endings in cinema history.

The Social Network [2010]

The film opens with Harvard University student Mark Zuckerberg dumped by his girlfriend Erica Albright. Later he hacked into college databases to steal photos of female students and created Facesmash to rate their attractiveness. The site caught the attention of the Winklevoss twins and their business partner who invited him to work on the Harvard Connection, a social dating network for Harvard students. From there it’s not much of a leap for Zuckerberg to create the social network phenomenon we know today as Facebook.

Penned by Aaron Sorkin, The Social Network features snappy dialogue set in the disquieting intense atmosphere of a David Fincher movie. The result is a visually arresting film of dark beauty. While it gives flashes on the contemporary fever of startup life, it has all the classic story elements of friendship, class, and betrayal - powerfully captured in this scene.

There you have it! We hope this list of movies will boost your imagination and stoke that fire in your gut once more. Happy watching!